Cyanate Esters (i.e., Compounds Having The -ocn Group Bonded Directly To Carbon, Which Carbon May Be Single Bonded To Any Atom But May Be Multiple Bonded Only To Carbon) Patents (Class 560/301)
  • Patent number: 10370569
    Abstract: A curable composition for bonding windings or core laminates in an electrical machine is presented. The curable composition includes: (A) about 10 weight percent to about 25 weight percent of a polyfunctional cyanate ester; (B) about 35 weight percent to about 65 weight percent of a first difunctional cyanate ester, or a prepolymer thereof; (C) about 15 weight percent to about 40 weight percent of a second difunctional cyanate ester, or a prepolymer thereof. An associated method is also presented.
    Type: Grant
    Filed: January 8, 2018
    Date of Patent: August 6, 2019
    Assignee: GENERAL ELECTRIC COMPANY
    Inventors: Weijun Yin, Gary William Yeager, Kevin Warner Flanagan, David Andrew Simon, Eugene Pauling Boden, Kathryn Amanda Misner
  • Patent number: 10338471
    Abstract: The composition for forming an underlayer film for lithography according to the present invention contains a compound represented by a specific formula (1) and 20 to 99% by mass of a solvent component (S), in which 27 to 100% by mass of the compound represented by the formula (1) is included in a component (A) other than the solvent component (S).
    Type: Grant
    Filed: July 31, 2015
    Date of Patent: July 2, 2019
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Kana Okada, Takashi Makinoshima, Masatoshi Echigo, Go Higashihara, Atsushi Okoshi
  • Patent number: 8633328
    Abstract: Provided are saturated partially fluorinated alkoxy carboxylic acids or salts thereof and methods of preparation.
    Type: Grant
    Filed: April 15, 2013
    Date of Patent: January 21, 2014
    Assignee: 3M Innovative Properties Company
    Inventors: Tilman C. Zipplies, Klaus Hintzer, Oleg Shyshkov
  • Publication number: 20130281640
    Abstract: There is provided a novel dicyanatophenyl-based difunctional cyanate ester which is in a liquid form at ordinary temperature and can obtain a cured product having an excellent low thermal expansion rate. There is disclosed a cyanate ester compound represented by the following formula (I): (wherein R1 represents a hydrocarbon group having 2 to 20 carbon atoms).
    Type: Application
    Filed: October 25, 2011
    Publication date: October 24, 2013
    Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Makoto Tsubuku, Taketo Ikeno, Masayuki Katagiri, Tomoo Tsujimoto
  • Publication number: 20130231494
    Abstract: Provided are saturated partially fluorinated alkoxy carboxylic acids or salts thereof and methods of preparation.
    Type: Application
    Filed: April 15, 2013
    Publication date: September 5, 2013
    Applicant: 3M Innovative Properties Company
    Inventors: Tilman C. Zipplies, Klaus Hintzer, Oleg Shyshkov
  • Publication number: 20110118429
    Abstract: Charge transport materials are provided, and methods for making the same.
    Type: Application
    Filed: December 23, 2005
    Publication date: May 19, 2011
    Applicant: E.I. DU PONT DE NEMOURS AND COMPANY
    Inventors: Nora Sabrina Radu, Norman A. Herron, Gary Johansson
  • Publication number: 20110009559
    Abstract: Aromatic dicyanate compounds which comprise aliphatic moieties having at least about six carbon atoms and resins and thermoset products based on these compounds.
    Type: Application
    Filed: March 9, 2009
    Publication date: January 13, 2011
    Applicant: Dow Global Technologies Inc.
    Inventors: Michael J. Mullins, Robert E. Hefner, Ulrich Herold, Mark B. Wilson
  • Patent number: 7674876
    Abstract: Novel hybrid monomers containing both the aryltrifluorovyinyloxyether-group (TFVE-group) and the cyanato-group, their synthesis, and the synthesis of polymers made from these new hybrid monomers are disclosed.
    Type: Grant
    Filed: May 24, 2006
    Date of Patent: March 9, 2010
    Assignees: Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V., Clemson University
    Inventors: Christian Dreyer, Monika Bauer, Suresh S. Iyer, Dennis W. Smith
  • Patent number: 7202378
    Abstract: The present invention relates to a process for producing 5-nitro-3,4-dihydro-1(2H)-naphthalinone, 1,5-naphthalenediamine and 1,5-naphthalene diisocyanate, in which 4-(2-nitrophenyl)-n-butyronitrile is converted to 4-(2-nitrophenyl)-n-butyric acid.
    Type: Grant
    Filed: April 7, 2006
    Date of Patent: April 10, 2007
    Assignee: Bayer MaterialScience AG
    Inventors: Joachim Zechlin, Kai Verkerk, Dietmar Wastian, Katrin Joschek, Tim Loddenkemper, Wilfried Pinke, Michael Schelhaas, Georg Ronge
  • Patent number: 6800721
    Abstract: The unsaturated oligophenol cyanates of the general formula [A—]n[B—A—]xB[—A]m   (I) in which A is a group of formula: and B is a group of formula: where R1, R2 and R3 are each hydrogen or a bond with a group B, there being either one or two bonds with group B; and both R4 and R4′ as well as R5 and R5′ separately or jointly represent a direct bond or hydrogen and a bond with a group A, there being either one or two bonds with A. The indices m and n are 0 or 1 but not both 1 at the same time and x is a whole number between 0 and 10, where at least one of the numbers, m, n and x is not 0. The unsaturated oligophenol cyanates can be prepared by reacting the corresponding oligophenols with cyanogen chloride. The have a low viscosity and owing to their double bonds are able to undergo free-radical polymerization.
    Type: Grant
    Filed: February 9, 2001
    Date of Patent: October 5, 2004
    Assignee: Lonza AG
    Inventors: Ulrich Daum, Alessandro Falchetto
  • Patent number: 6603035
    Abstract: Provided is a method for producing high purity cyanate derived from a phenol compound represented by the following formula (I): in the formula, each of A independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, X represents a single bond, an organic group having 1 to 20 carbon atoms, a carbonyl group, a sulfone group, a divalent sulfur atom or an oxygen atom, i and n represent an integer from 0 to 4. The cyanate contains low amount of impurities such as unreacted phenols and imidecarbonate, and is preferably used as a thermosetting resin for a sealing, laminate, composite material, molding material and adhesive for electric parts.
    Type: Grant
    Filed: August 20, 1999
    Date of Patent: August 5, 2003
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Satoshi Okamoto, Hisashi Watabu
  • Patent number: 6458993
    Abstract: The present invention relates to novel aromatic cyanate ester compounds containing at least two rings linked by a group containing an unsaturated group. The present invention further relates to compositions and prepolymers of said novel aromatic cyanate ester compounds. The present invention further relates to a process for preparing said compounds and cured articles resulting from curable mixtures thereof.
    Type: Grant
    Filed: January 31, 2001
    Date of Patent: October 1, 2002
    Assignee: Vantico Inc.
    Inventors: Bor-Sheng Lin, Michael James Amone
  • Patent number: 6380344
    Abstract: A cyanate ester-epoxy resin composition that can be cured to obtain a product which has excellent mechanical properties is provided. More particularly, a cyanate ester composition comprising (A) a cyanate ester in which the total content of impurities containing imino carbonates, alkyl cyanamides, partially substituted cyanates and phenols is 5% or less, or a prepolymer thereof and (B) an epoxy resin is provided.
    Type: Grant
    Filed: May 11, 1999
    Date of Patent: April 30, 2002
    Assignee: Sumitomo Chemical Company, Ltd.
    Inventors: Toshiaki Hayashi, Nobuyuki Nakajima
  • Patent number: 6365671
    Abstract: The present invention relates to compositions of matter containing aromatic cyanate ester containing at least two rings linked by a group containing an unsaturated group and selected aromatic hydroxyl compounds that exhibited improved heat release and curing properties. The present invention further relates to a process for preparing said compounds and cured articles resulting from curable mixtures thereof.
    Type: Grant
    Filed: June 26, 2000
    Date of Patent: April 2, 2002
    Assignee: Vantico Inc.
    Inventors: Bor-Sheng Lin, Michael James Amone
  • Patent number: 6217943
    Abstract: A composition of matter comprises an aromatic cyanate ester silane comprising at least one cyanate ester group and at least one hydrolyzable silyl group. In the presence of a cyanate ester resin the aromatic cyanate ester silane acts as a coupling agent to improve the adhesion of the cyanate ester to a substrate. The curable compositions are useful as reinforced composites, and as adhesive and coating compositions.
    Type: Grant
    Filed: April 5, 1999
    Date of Patent: April 17, 2001
    Assignee: 3M Innovative Properties Company
    Inventors: Joyce B. Hall, Fred B. McCormick, Kim M. Vogel, Hiroyaki Yamaguchi
  • Patent number: 6150001
    Abstract: Reactive monomers of cyanate esters are vapor deposited onto thin film disks used for magnetic recording. The monomer films are then irradiated with ultraviolet (UV) light to polymerize the deposited monomer to form a solid, robust polycyanate ester overlayer on the disk that becomes smoother, more corrosion resistant and, when lubricated, more durable than disks without the overlayer. The polycyanate ester overlayer can either replace the conventional carbon overcoat or allow a substantially thinner carbon overcoat to be used.
    Type: Grant
    Filed: March 30, 1998
    Date of Patent: November 21, 2000
    Assignee: International Business Machines Corporation
    Inventors: James Lupton Hedrick, Charles Mathew Mate, Junhua Wu
  • Patent number: 6121484
    Abstract: Arylcyanates are produced by reacting polyvalent phenols with a halogen cyanogen in the presence of a tertiary amine and a nonaqueous solution at high temperature. The tertiary ammonium halogenide obtained as a secondary product is fully or partially removed by processing the reaction mixture with cationic and anionic exchanger, whereby arylcyanates with a particularly low halogenide content are obtained.
    Type: Grant
    Filed: May 21, 1999
    Date of Patent: September 19, 2000
    Assignee: Lonza AG
    Inventor: Alessandro Falchetto
  • Patent number: 5932762
    Abstract: A process for the production of aryl cyanates of the general formula I: ##STR1## A phenol of the general formula II: ##STR2## a tertiary amine and cyanogen chloride, of which at least one of the three components is present as a solution in an organic solvent, are fed essentially simultaneously and continuously at a temperature of -20.degree. C. to 0.degree. C. and in a molar ratio of cyanogen chloride to the reactive hydroxy groups of the phenol of 1.0:1.0 to 1.2:1.0 in a cooled loop reactor, so that the reaction components, before they come in contact with one another, are prediluted by the reaction mixture circulating in the loop reactor. Simultaneously, a stream of the reaction mixture corresponding to the fed volume of the reaction components is drawn off from the circulation.
    Type: Grant
    Filed: January 8, 1997
    Date of Patent: August 3, 1999
    Assignee: Lonza, Ltd.
    Inventors: Alessandro Falchetto, Ulrich Daum
  • Patent number: 5912377
    Abstract: A composition of matter comprises an aromatic cyanate ester silane comprising at least one cyanate ester group and at least one hydrolyzable silyl group. In the presence of a cyanate ester resin the aromatic cyanate ester silane acts as a coupling agent to improve the adhesion of the cyanate ester to a substrate. The curable compositions are useful as reinforced composites, and as adhesive and coating compositions.
    Type: Grant
    Filed: June 5, 1996
    Date of Patent: June 15, 1999
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Joyce B. Hall, Kim M. Vogel, Fred B. McCormick, Hiroyaki Yamaguchi
  • Patent number: 5866711
    Abstract: Fluorinated vinyl ethers having cyanate or carbamate groups are useful as monomers in making fluoropolymers having functional sites.
    Type: Grant
    Filed: July 23, 1997
    Date of Patent: February 2, 1999
    Assignee: E. I. du pont de Nemours and Company
    Inventors: Ming-Hong Hung, Paul Douglas Brothers, Dewey Lynn Kerbow
  • Patent number: 5648445
    Abstract: Allophanate-modified 1,3-phenylene diisocyanates or 1,1-biphenyl diisocyanates or 1,1'-oxy-bis-(isocyanato benzenes) which are storage stable liquid at 25.degree. C. are made by reacting the diisocyanate and a mono-alcohol to form an isocyanate containing urethane groups. The urethane groups in the diisocyanate are then converted to allophanate groups. The resultant product which has an isocyanate group content of from about 10 to about 40% may be further reacted with isocyanate-reactive compounds to produce an allophanate-modified diisocyanate prepolymer containing urethane or urea groups having an isocyanate group content of from about 5 to about 40.0%. The liquid, storage-stable, allophanate-modified diisocyanates produced by these processes are particularly useful in the production of elastomers and flexible foams.
    Type: Grant
    Filed: December 22, 1995
    Date of Patent: July 15, 1997
    Assignee: Bayer Corporation
    Inventors: William E. Slack, Rick L. Adkins
  • Patent number: 5563237
    Abstract: A cyanate resin composition suitable for a copper-clad laminate comprises components (A) and (B).(A) a cyanate compound of the formula: ##STR1## wherein R and Q each represents halogen, C.sub.1-10 alkyl, C.sub.5-7 cycloalkyl or C.sub.6-20 hydrocarbon; i and j each represents 0-4 and M is (2): ##STR2## wherein T represents halogen, C.sub.1-10 alkyl, C.sub.5-7 cycloalkyl or C.sub.6-20 hydrocarbon; k represents 0-10 and m represents 0-8, and(B) a hardener.
    Type: Grant
    Filed: February 23, 1994
    Date of Patent: October 8, 1996
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yasuhiro Endo, Yoichi Ueda, Toshiaki Hayashi, Mitsuhiro Shibata, Shinichiro Kitayama, Shuichi Kanagawa, Hisashi Watabu
  • Patent number: 5550282
    Abstract: Dislcosed is a curable composition of a partially trimerized prepolymer of the dicyanate ester of the formula ##STR1## wherein R.sub.1 and R.sub.2 are the same or different and each is alkyl, perfluoroalkyl, aryl or halogen; and A is a bridge selected from the group consisting of a direct bond, methylene optionally mono- or disubstituted by alkyl, perfluoroalkyl and/or aryl, a five or six membered cycloalkylene, sulfonyl, thio, oxy, carbonyl, phenylene, and xylylene optionally substituted by alkyl at on or both methylene carbon atoms is useful in the manufacture of electrical laminates having excellent dielectric properties in the GHz region.
    Type: Grant
    Filed: July 13, 1994
    Date of Patent: August 27, 1996
    Assignee: Kanegafuchi Kagaku Kogyo Kabushiki Kaisha
    Inventors: Hidenari Tsunemi, Toshinobu Nakata
  • Patent number: 5488144
    Abstract: A novel dicyanate ester of the formula: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are the same or different and each is hydrogen, alkyl, perfluoroalkyl, aryl or halogen; A is a bridge selected from the group consisting of direct bond, methylene optionally mono- or di-substituted by alkyl, perfluoroalkyl and/or aryl, a five or six membered cycloalkylene, sulfonyl, thio, oxy, carbonyl, phenylene, and xylylene optionally substituted by alkyl at one or both methylene carbon atoms; with the proviso that when the cyanato group is at the para-position relative to the bridge A, both R.sub.1 and R.sub.2 are not hydrogen, and its prepolymer are useful in the manufacture of electrical laminates having excellent dielectric properties in GHz region.
    Type: Grant
    Filed: April 15, 1994
    Date of Patent: January 30, 1996
    Assignee: Kanegafuchi Kagaku Kogyo Kabushiki Kaisha
    Inventors: Hidenari Tsunemi, Toshinobu Nakata
  • Patent number: 5420342
    Abstract: Bis(4-cyanatophenyl)-1,1-ethane, a low viscosity liquid, which is useful in wet filament winding, resin transfer molding and pultrusion processes is made by reacting cyanogen chloride dissolved in methylisobutylketone with a methylisobutylketone solution of bis(4-hydroxylphenyl)-1,1-ethane and a tertiary amine.
    Type: Grant
    Filed: November 19, 1993
    Date of Patent: May 30, 1995
    Assignee: Ciba-Geigy Corporation
    Inventor: Wallace M. Craig, Jr.
  • Patent number: 5374769
    Abstract: Novel polycyanate compositions containing one or more mesogenic moieties as lateral substituents are disclosed which provide improved processability relative to polycyanates containing one or more mesogenic moieties in the main chain of the molecule. Molecular level ordering of the resulting thermosets is maintained much similar to that found thermosets of polycyanates which have one or more mesogenic moieties in the main chain.
    Type: Grant
    Filed: December 24, 1992
    Date of Patent: December 20, 1994
    Assignee: The Dow Chemical Company
    Inventors: Robert E. Hefner, Jr., Jimmy D. Earls
  • Patent number: 5360887
    Abstract: A flame-retarded thermosetting resin composition is provided by blending about 5 to 45 mole % of a phenylcyanate having at least one halogen substituent at the ortho or para position relative to the cyanato group, and about 55 to 95 mole % of a halogen-free bis-4-phenylcyanate. A flame retardancy of V-O grade of UL94 is achieved in the thermoset resin of the composition without compromising dielectric, heat resistance, moisture absorption and other properties.
    Type: Grant
    Filed: July 28, 1993
    Date of Patent: November 1, 1994
    Assignee: Kanegafuchi Kagaku Kogyo Kabushiki Kaisha
    Inventors: Hidenari Tsunemi, Toshinobu Nakata, Koyoyuki Namura
  • Patent number: 5340912
    Abstract: A cyanate-functional compound is provided which can be described by the formula ##STR1## in which Ar is a C.sub.6-20 aromatic moiety, L is a hexanenorbornane linking moiety, L' is a divalent cycloaliphatic moiety, and each of m and n is a number within the range of 0 to about 10. Such cyanate esters include the product of cyanation of the addition reaction of a phenol with a cyclohexene norbornene compound such as 5-(3-cyclohexen-1-yl)bicyclo[2.2.1]hept-2-ene. The resulting cyanate esters have low melt viscosity and low water absorbance in the cured state and are useful as the resinous component of high-performance electrical laminating and encapsulation formulations.
    Type: Grant
    Filed: February 23, 1993
    Date of Patent: August 23, 1994
    Assignee: Shell Oil Company
    Inventors: Pen-Chung Wang, Donald R. Kelsey
  • Patent number: 5292861
    Abstract: Trisphenol PA tricyanate, prepolymers and crosslinked polymers thereof are provided. Blends of trifunctional cyanates and fluorinated or non-fluorinated difunctional cyanate are provided. The crosslinked polymers exhibit low dielectric loss properties and high glass transition temperatures and are suitable as the matrix material for structural composites including printed circuit boards.
    Type: Grant
    Filed: December 29, 1992
    Date of Patent: March 8, 1994
    Assignee: International Business Machines Corporation
    Inventor: Konstantinos I. Papathomas
  • Patent number: 5284968
    Abstract: Bis(4-cyanatophenyl)-1,1-ethane, a low viscosity liquid, which is useful in wet filament winding, resin transfer molding and pultrusion processes is made by reacting cyanogen chloride dissolved in methylisobutylketone with a methylisobutylketone solution of bis(4-hydroxylphenyl)-1,1-ethane and a tertiary amine.
    Type: Grant
    Filed: September 30, 1991
    Date of Patent: February 8, 1994
    Assignee: Ciba-Geigy Corporation
    Inventor: Wallace M. Craig, Jr.
  • Patent number: 5162574
    Abstract: Bis(4-cyanatophenyl)-1,1-ethane, a low viscosity liquid, is useful in wet filament winding, resin transfer molding and pultrusion processes.
    Type: Grant
    Filed: September 13, 1990
    Date of Patent: November 10, 1992
    Assignee: Hi-Tek Polymers, Inc.
    Inventor: Wallace M. Craig, Jr.
  • Patent number: 5149863
    Abstract: Cyanate esters of 4,4'-[1,3-phenylenebis(1-methylethylidene)] 2,2',6,6'-R-bisphenol when properly catalyzed, can be cured at temperatures in the range of about 250.degree. to about 300.degree. F. to obtain percent cyclotrimerization of the cyanate ester groups of at least 80 percent.
    Type: Grant
    Filed: August 12, 1991
    Date of Patent: September 22, 1992
    Assignee: Hi-Tek Polymers, Inc.
    Inventors: David A. Shimp, Jeffrey T. Vanderlip
  • Patent number: 5142081
    Abstract: This present invention relates to a process for the preparation of O-silylated aliphatic hydroxyl, compounds by the reaction of aliphatic hydroxyl compounds with triorganochlorosilanes and removal of the resulting gaseous hydrogen chloride from the reaction mixture, characterized in that the reaction is carried out in the presence of phase transfer catalysts in the absence of solvent.The invention also relates to the use of the O-silylated hydroxyl compounds obtained by this process as starting materials for the preparation of isocyanates containing ester groups by a reaction with isocyanato carboxylic acid chlorides.
    Type: Grant
    Filed: October 10, 1990
    Date of Patent: August 25, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Lutz Schmalstieg, Josef Pedain, Klaus Nachtkamp
  • Patent number: 5130454
    Abstract: Polytetrahydrofuran derivatives of the general formula ##STR1## where n is from 2 to 70, X is the bridge member --NH-- or --O-- and R.sup.1 and R.sup.4 are each hydrogen or various radicals.
    Type: Grant
    Filed: December 19, 1990
    Date of Patent: July 14, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Eckhard Hickmann, Ulrich Koehler, Hardo Siegel
  • Patent number: 5089660
    Abstract: A comonomer composition of an aromatic polycyanate and an aromatic monocyanate substituted at each position ortho to the cyanate group, and a polytriazine copolymer derived therefrom.
    Type: Grant
    Filed: January 22, 1988
    Date of Patent: February 18, 1992
    Assignee: The Dow Chemical Company
    Inventors: Daniel J. Murray, Mitchell G. Dibbs, Philip C. Yang
  • Patent number: 5068309
    Abstract: Cyanate esters of 4,4'-[1,3-phenylenebis (1-methylethylidene)] 2,2',6,6'-R-bisphenol when properly catalyzed, can be cured at temperatures in the range of about 250.degree. to about 300.degree. F. to obtain percent cyclotrimerization of the cyanate ester groups of at least 80 percent.
    Type: Grant
    Filed: March 29, 1990
    Date of Patent: November 26, 1991
    Assignee: Hi-Tek Polymers, Inc.
    Inventors: David A. Shimp, Jeffrey T. Vanderlip
  • Patent number: 4983709
    Abstract: New aromatic compounds containing at least one cyanate ester and at least one propargyl ether group, each independently directly attached to a ring carbon atom(s), are useful in the preparation of resins having a low dielectric constant.
    Type: Grant
    Filed: December 2, 1988
    Date of Patent: January 8, 1991
    Assignee: Shell Oil Company
    Inventor: Roy J. Jackson
  • Patent number: 4981994
    Abstract: A base-catalyzed process is provided for the preparation of cyanate esters, the process including the step of pre-reacting a phenolic starting material with the basic catalyst and then reacting the pre-reaction product with a cyanogen halide. The process permits the preparation of cyanate esters in high yields at reaction temperatures above room temperature.
    Type: Grant
    Filed: July 31, 1989
    Date of Patent: January 1, 1991
    Assignee: Shell Oil Company
    Inventor: Roy J. Jackson
  • Patent number: 4944373
    Abstract: An asbestos-free disc brake pad is provided by employing a cyanate ester-based resin composition as binder. The disc brake pad exhibits consistent braking properties over a wide range of operating temperatures and an improved service life. Also the serious pollution problem due to use of asbestos in the conventional brake pads is removed.
    Type: Grant
    Filed: June 1, 1989
    Date of Patent: July 31, 1990
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Kazuyuki Ohya, Hidenori Kimbara
  • Patent number: 4940848
    Abstract: Stable prepolymer solutions are made from partially cyclotrimerized 4,4'-thiodi(phenylcyanate) dissolved in cyclopentanone. The prepolymer solutions are used to make flame retardant and thermally stable laminates.
    Type: Grant
    Filed: November 10, 1988
    Date of Patent: July 10, 1990
    Assignee: Hi-Tek Polymers, Inc.
    Inventor: David A. Shimp
  • Patent number: 4839442
    Abstract: Low viscosity dicyanate esters are made from bisphenols wherein the bridging member between the phenyl groups is unsymmetrical. These dicyanate esters are blended with prepolymers of dicyanate esters to form low viscosity non-crystallizing resins useful in preparing composites.
    Type: Grant
    Filed: June 20, 1988
    Date of Patent: June 13, 1989
    Assignee: Hi-Tek Polymers, Inc.
    Inventor: Wallace M. Craig, Jr.
  • Patent number: 4820855
    Abstract: A process for producing a polyfunctional cyanate ester polymer which comprises heating at least one polyfunctional cyanate ester compound having the formula:R--OCN).sub.mwherein m is an integer of at least 2 and R is one or more aromatic organic groups, and the cyanato groups are bonded to the arylene ring, in the presence of a catalytic amount of a dialkyl tin oxide having the formula:R.sup.1 R.sup.2 SnOwherein each of R.sup.1 and R.sup.2 is C.sub.1 -C.sub.30 alkyl is disclosed.
    Type: Grant
    Filed: October 16, 1987
    Date of Patent: April 11, 1989
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Morio Gaku, Hidenori Kimbara
  • Patent number: 4782178
    Abstract: Phenyl cyanates substituted at both ortho positions and further substituted with at least one halo at the meta or para positions are prepared. Then enhance ignition resistance, fire retardance, and toughness of polytriazines when added in varying amounts to polycyanate monomers before cure.
    Type: Grant
    Filed: November 13, 1987
    Date of Patent: November 1, 1988
    Assignee: The Dow Chemical Company
    Inventors: James P. Godschalx, Daniel J. Murray, Abel Mendoza
  • Patent number: 4752648
    Abstract: Chlorophosphines or thiophosphinic acid chlorides of the general formulae RPCl.sub.2, R.sub.2 PCl or R.sub.2 P(.dbd.S)Cl are made from feed materials selected from hydrogen-functional primary or secondary phosphines or secondary phosphine sulfides, where R stands for identical or different, linear or branched, substituted or unsubstituted alkyl radicals having from 1-16 carbon atoms, aryl radicals, aralkyl radicals or alkylaryl radicals having from 6-9 carbon atoms or cycloalkyl radicals having from 5-10 carbon atoms. To this end, the feed materials are reacted with phosphorus pentachloride, or with chlorine gas in the presence of phosphorus trichloride at temperatures within the range -78.degree. to +145.degree. C. It is possible for two radicals R to be linked together by one or two substituted or unsubstituted hydrocarbon chains having from 1-4 carbon atoms.
    Type: Grant
    Filed: September 18, 1986
    Date of Patent: June 21, 1988
    Inventors: Norbert Weferling, Werner Klose
  • Patent number: 4751323
    Abstract: This invention relates to a polyaromatic cyanate which corresponds to the formula ##STR1## wherein Ar is an aromatic radical;B is a C.sub.7-20 polycyclic aliphatic radical;D is independently in each occurrence any non-active hydrogen-containing substituent;q, r and s are independently in each occurrence the integers b 0, 1, 2, l or b 3l ; with the proviso that the sum of q, 4 and s is greater than or equal to 2;t is independently in each occurrence an integer of between about 0 and 4 inclusive; andx is a number between about 0 and 5 inclusive.Another aspect of this invention is a novel polytriazine which comprises the reaction product of the polyaromatic cyanate esters of this invention. The novel polytriazines may further comprise the reaction product of the novel polyaromatic cyanates of this invention in admixture with other cyanates known in the art as useful for the preparation of polytriazines.
    Type: Grant
    Filed: November 16, 1983
    Date of Patent: June 14, 1988
    Assignee: The Dow Chemical Company
    Inventors: Edmund P. Woo, Daniel J. Murray
  • Patent number: 4748270
    Abstract: A process for the preparation of an aromatic cyanate which comprises (a) preparing in situ a cyanogen chloride by contacting a solution of chlorine in a chlorinated hydrocarbon with an aqueous solution of an alkali metal cyanide at a temperature of 0.degree. C. or below under conditions such that a cyanogen chloride is prepared; (b) physically separating the chlorinated hydrocarbon in which the cyanogen chloride is dissolved from the aqueous layer in which an alkali metal chloride salt is dissolved; and (c) contacting the cyanogen chloride dissolved in the chlorinated hydrocarbon with a hydroxy-substituted aromatic compound dissolved in a chlorinated hydrocarbon, a secondary alcohol or a tertiary alcohol, in the presence of a tertiary amine at a temperature of about 0.degree. C. or less under conditions such that a polyaromatic cyanate is prepared.
    Type: Grant
    Filed: November 16, 1983
    Date of Patent: May 31, 1988
    Assignee: The Dow Chemical Company
    Inventors: Daniel J. Murray, Edmund P. Woo
  • Patent number: 4745215
    Abstract: 4,4'-(Hexafluoroisopropylidene) bisphonol dicyanate and related compounds have reduced dielectric constant, reduced moisture absorption, and increase Tg making such compounds especially suitable for various electronic applications, such as circuit packaging or in forming prepregs and circuit boards.
    Type: Grant
    Filed: April 3, 1987
    Date of Patent: May 17, 1988
    Assignee: International Business Machines Corporation
    Inventors: Robert J. Cox, William J. Summa, David W. Wang
  • Patent number: 4647582
    Abstract: A compound of the formula: ##STR1## useful as a fungicidal agent against phytopathogenic fungi, and particularly against strains resistant to benzimidazole, thiophanate and/or cyclic imide fungicides.
    Type: Grant
    Filed: December 23, 1983
    Date of Patent: March 3, 1987
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Junya Takahashi, Toshiro Kato, Hiroshi Noguchi, Yukio Oguri, Shigeo Yamamoto, Katsuzo Kamoshita
  • Patent number: 4612359
    Abstract: Thermosettable compositions are prepared which contain (A) from about 0.1 to 100 percent by weight of an esterified aromatic cyanate; (B) from zero to about 99.9 percent by weight of an aromatic polycyanate, an aromatic polycyanamide or mixture thereof and (C) from zero to about 99.9 percent by weight of an epoxy resin.
    Type: Grant
    Filed: October 16, 1985
    Date of Patent: September 16, 1986
    Assignee: The Dow Chemical Company
    Inventor: Robert E. Hefner, Jr.